Is Biobased the New Highway to the Old Nylon?

We reproduce below an excellent article from BioFuels Digest written by Jim Lane on the state of the development of bio-based nylon intermediates and specifically progress made in this field by US based bio-tech company Genomatica. The style is exhilarating and I wish you an enjoyable reading.

If you get hip to this nylon tip, and take a California trip, you’ll get a kick from Genomatica’s new route to 6,6.

From California, we’ve learned that Genomatica is going public with its third development program, entering into the world of biobased nylon intermediates – after its success in licensing its BDO process to BASF and Novamont with Invista, DSM, Lanxess, Toray, and Far Eastern New Century working up commercialization plans; and progress with butadiene, with Versalis and Braskem as partners, and over $100 million in industry support.

Route 6,6 is a little less euphonically memorable than the Route 66 of film and song: instead of “St. Louie down to Missouri, and Oklahoma city looks oh so pretty,” we have hexamethylenediamine, caprolactam and adipic acid, which are generally known as HMD, CPL and ADA, and that’s about as sexy as anyone has made it to date.

Generally HMD and adipic acid are the ingredients in nylon 6,6 (also known as PA 6,6), while CPL is the key ingredient in nylon 6.

Of course, the numbers are a little more attractive. The three of them represent a total market of over $18 billion per year, which is the GDP of Honduras, and that’s a lot of polymer. Fans of the artist Christo might note that you could cover Latvia with that much nylon fabric. (Yes, purists, Christo generally worked with polypropylene, but you get the idea).

Nylon and Energy Security

Generally speaking, when we talk about “getting off petroleum” and energy security, we’re talking about fuels — for one, it’s a huge market and, for two, you pump something liquid into your car and the link to petroleum is obvious and, well, it feels expensive as you watch the dials spin up the cost faster than you can shout “come on, big money” to a slot-machine wheel in Vegas.

But nylon is a pretty giant consumer of petroleum — courtesy of the fact that it takes roughly 5 pounds of oil to make a pound of nylon. So, think, 25+ million tons of oil, or 1.5 billion gallons if you’d prefer the liquid measure. That’s roughly the gasoline demand in Nevada, speaking of Vegas.

So, while energy security hawks haven’t been targeting carpets, it’s not an entirely bad place to take the “war on imported petroleum” forward.

Nylon and the Biobased Rush

Genomatica’s nylon intermediates program aims to deliver biobased processes for the production of hexamethylenediamine, caprolactam and adipic acid (HMD, CPL and ADA).

Nylon has been a hot target for biobased companies in recent years, despite weaker business conditions for caprolactam that DSM recently reported in its Q2 results announce, primarily because of the price volatility and supply constraints associated with benzene or adiponitrile — made primarily from your friend petroleum. Not to mention the sustainability issues associated with unwanted byproducts and waste streams characteristic of many current processes.

For those of you in the “why make a $3 fuel when you can make a $5 chemical,” nylon is the $10 chemical, with global prices hovering in the $1.60 per pound range. DSM just recently announced a hefty price hike on nylon 6, and plans to build a nylon 6 plant in North America.

The competition is pretty fierce and the nylon resins field is crowded with the major players, all looking for an edge. DuPont remains a major player after having invented nylon back in the 1930s; Invista is huge, Lanxess, Honeywell, Solvay Honeywell, the afore-mentioned DSM, too.

On the biobased side — so far we have seen the most noise from BASF, which in May introduced a biobased nylon from renewable raw materials under its Ultramid brand.

Nylon of course has a highly-established market in a host of consumer and industrial applications from fabric to toothbrushes and carpet fiber — and just about every company that has been targeting biobased succinic acid has had its eye on adipic.

Caprolactam has been a rarer target — to date, only Joule Unlimited and BioAmber have disclosed publicly that they are in pursuit, and Joule is some distance from commercial-scale production and has more than 80 molecules in its disclosed targets — so, caprolactam fiends may well have to look elsewhere for some time.

HMD is a little more popular. Not only does BioAmber have it on the list, Rivertop Renewables recently disclosed an interest, and Rennovia is all over it in its quest to make RENNLON, its 100% biobased nylon 6,6 polymer.

In the short term, it may be that Rennovia proves to be the most formidable competitor to Genomatica in the quest for nylon. Last year,w e reported that “Production costs for Rennovia’s bio-based AA and HMD are projected to be 20-25% below that of conventional petroleum-based AA and HMD, with a significantly lower per-pound capital cost. Additional projected benefits include an 85% reduction in greenhouse gas emissions compared to conventional petroleum-derived AA, and a 50% reduction in GHG emissions compared to conventional petroleum-derived HMD.”

Not to mention the $25M investment that Rennovia recently hauled in from Archer Daniels Midland in February.

In Genomatica’s corner? The company’s integrated biotechnology platform, which combines process engineering, predictive computer models, and its experimental biotechnology. Not to mention its established array of customers in BDO and increasingly on the butadiene side.

Specifically, the nylon program builds on a large body of intellectual property (IP), which includes but is not limited to eight issued U.S. patents and numerous pending applications worldwide, as well as trade secrets that include engineered strains, with some of the IP developed internally and some from a recent IP acquisition. A number of the concepts described by Genomatica’s patent filings have been validated in experimental proofs of concept, demonstrating feasibility. These include the successful demonstration of certain metabolic pathways; production of certain nylon intermediates in various microorganisms; and efficient methods to produce and recover certain nylon intermediates from the fermentation.

For now, Genomatica is recruiting development partners, who have the opportunity to engage throughout the program, influence priorities and gain early access to the resulting process technology.